三种富含萜类植物的化学成分研究
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摘要
本文系统报道了三种富含萜类成分植物的次生代谢产物研究,包括樟科(Lauraceae)植物乌药(Lindera aggregata),杜鹃花科(Ericaceae)植物黄毛杜鹃(Rhododendron rufum Batalin),菊科(Compositae)植物南美蟛蜞菊(Wedelia trilobata)。樟科植物乌药为传统常用中药,是重要的温胃理气止痛药之一,用于治疗脘腹胀痛、痛经、寒疝及膀胱虚寒引起的小便频数、遗尿等；杜鹃科植物黄毛杜鹃是我国中西部的著名观赏植物；菊科植物南美蟛蜞菊是20世纪70年代引入我国的入侵性植物,民间主要用其来治疗蛇伤、鱼伤、腹泻、肾结石、感冒等疾病。
采用常规的萃取、硅胶柱层析(CC)、制备薄层层析(PTLC)、重结晶等手段分离得到了62个化合物。利用各种现代波谱技术(IR、UV、CD、EIMS、ESIMS、HRESIMS、1HNMR、13CNMR、DEPT-135、NOEDS、1H-1H COSY、HSQC、HMBC)及X-ray单晶衍射分析法,确定了化合物的结构,其中8个为新化合物。从乌药中得到21个化合物,其中7个为新化合物；从黄毛杜鹃中得到27个化合物；从南美蟛蜞菊中分离得到14个化合物,其中1个为新化合物。其中我们利用CD法确定了化合物La3, La4,和La5的绝对构型。
我们从入侵植物角度出发,通过文献调研,从植物激素、化感作用两方面,结合南美蟛蜞菊化学成分研究的结果,分析并阐述了南美蟛蜞菊化学成分研究的生态学意义,贝壳杉烷型二萜类化合物可能是南美蟛蜞菊具有强入侵性的重要原因。为保护生态平衡以及植物源农药的开发提供新的思路。
我们对山胡椒属植物1920年至今的化学成分研究报道进行了系统的综述,内容包括化学成分、生物活性以及该属植物的研究地域,表明了山胡椒属植物中次生代谢产物的结构多样性和其生物活性的多样性。
论文最后,我们通过文献调研,总结了萜类化合物在樟科、杜鹃花科、菊科中的分布,为这三个科萜类化合物的研究以及分类学的进一步发展和完善提供一些参考和帮助。
Three plants, which are rich in terpenoids, have been systematically investigated from phytochemical viewpoint, including Lindera aggregata (Lauraceae), Rhododendron rufum Batalin (Ericaceae), and Wedelia trilobata (Compositae). Lindera aggregata is an important medical plant and its root tubers are used as traditional Chinese herbs for the treatment of renal, cystic, and rheumatic diseases. Rhododendron rufum Batalin is a well-known ornamental plant in central and western China. Wedelia trilobata is an invasive plant and has been mainly used for the treatment of snakebite, fish injury, diarrhea, kidney stones, colds and other diseases.
There have been 62 compounds, including 8 new compounds, isolated from the three plants by means of silica gel column chromatography (CC), preparative thin layer chromatography (PTLC), and recrystallization etc. There are 21 compounds of these secondary metabolites obtained from Lindera aggregata,27 compounds from Rhododendron rufum Batalin, and 14 compounds from Wedelia trilobata. The structures of these compounds were elucidated by extensive spectroscopic methods, including IR, UV, CD, EIMS, HRESIMS,1H NMR,13C NMR, DEPT-135, NOEDS,1H-1H COSY, HSQC, HMBC, and X-ray single-crystal crystallography. In addition, the absolute configuration of compounds La3, La4, and La5 have been determined based on CD spectra analysis.
The ecological significance of phytochemical study on Wedelia trilobata was discussed. A detailed literature research, together with our experiment results, indicated that the kaurane diterpenoids may be an important factor contributing to its strong invasiveness. We hope this conclusion can provide references for the ecological blance and the development of botanical pesticides.
We summarized the secondary metabolites from the genus Lindera reported during the period of 1920-2011 as well as the biological activities assigned to this genus during the same period, which indicated the genus Lindera may be a rich source of substances with structral and biological diversity.
Finally, we summarized the distribution of terpenoids in the family Lauraceae, Ericaceae, and Compositae, which will be useful for the further study on terpenoids and development of chemotaxonomy of these families.
采用常规的萃取、硅胶柱层析(CC)、制备薄层层析(PTLC)、重结晶等手段分离得到了62个化合物。利用各种现代波谱技术(IR、UV、CD、EIMS、ESIMS、HRESIMS、1HNMR、13CNMR、DEPT-135、NOEDS、1H-1H COSY、HSQC、HMBC)及X-ray单晶衍射分析法,确定了化合物的结构,其中8个为新化合物。从乌药中得到21个化合物,其中7个为新化合物；从黄毛杜鹃中得到27个化合物；从南美蟛蜞菊中分离得到14个化合物,其中1个为新化合物。其中我们利用CD法确定了化合物La3, La4,和La5的绝对构型。
我们从入侵植物角度出发,通过文献调研,从植物激素、化感作用两方面,结合南美蟛蜞菊化学成分研究的结果,分析并阐述了南美蟛蜞菊化学成分研究的生态学意义,贝壳杉烷型二萜类化合物可能是南美蟛蜞菊具有强入侵性的重要原因。为保护生态平衡以及植物源农药的开发提供新的思路。
我们对山胡椒属植物1920年至今的化学成分研究报道进行了系统的综述,内容包括化学成分、生物活性以及该属植物的研究地域,表明了山胡椒属植物中次生代谢产物的结构多样性和其生物活性的多样性。
论文最后,我们通过文献调研,总结了萜类化合物在樟科、杜鹃花科、菊科中的分布,为这三个科萜类化合物的研究以及分类学的进一步发展和完善提供一些参考和帮助。
Three plants, which are rich in terpenoids, have been systematically investigated from phytochemical viewpoint, including Lindera aggregata (Lauraceae), Rhododendron rufum Batalin (Ericaceae), and Wedelia trilobata (Compositae). Lindera aggregata is an important medical plant and its root tubers are used as traditional Chinese herbs for the treatment of renal, cystic, and rheumatic diseases. Rhododendron rufum Batalin is a well-known ornamental plant in central and western China. Wedelia trilobata is an invasive plant and has been mainly used for the treatment of snakebite, fish injury, diarrhea, kidney stones, colds and other diseases.
There have been 62 compounds, including 8 new compounds, isolated from the three plants by means of silica gel column chromatography (CC), preparative thin layer chromatography (PTLC), and recrystallization etc. There are 21 compounds of these secondary metabolites obtained from Lindera aggregata,27 compounds from Rhododendron rufum Batalin, and 14 compounds from Wedelia trilobata. The structures of these compounds were elucidated by extensive spectroscopic methods, including IR, UV, CD, EIMS, HRESIMS,1H NMR,13C NMR, DEPT-135, NOEDS,1H-1H COSY, HSQC, HMBC, and X-ray single-crystal crystallography. In addition, the absolute configuration of compounds La3, La4, and La5 have been determined based on CD spectra analysis.
The ecological significance of phytochemical study on Wedelia trilobata was discussed. A detailed literature research, together with our experiment results, indicated that the kaurane diterpenoids may be an important factor contributing to its strong invasiveness. We hope this conclusion can provide references for the ecological blance and the development of botanical pesticides.
We summarized the secondary metabolites from the genus Lindera reported during the period of 1920-2011 as well as the biological activities assigned to this genus during the same period, which indicated the genus Lindera may be a rich source of substances with structral and biological diversity.
Finally, we summarized the distribution of terpenoids in the family Lauraceae, Ericaceae, and Compositae, which will be useful for the further study on terpenoids and development of chemotaxonomy of these families.
引文
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